1.1: isopropylmagnesium chloride / diethyl ether; tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 1.3: 0.5 h / 20 °C 2.1: diethyl ether / 20 °C 3.1: bis(dibenzylideneacetone)-palladium(0); bis[2-(diphenylphosphino)phenyl] ether; potassium tert-butylate / toluene / 100 °C / |Schlenk technique; |Inert atmosphere View Scheme

bromine; sodium hydrogensulfite in P2 O5; acetic acid

N-iodo-succinimide in various solvent(s) T=27°C; 0.416667 h;

1: 90 percent / NBS / various solvent(s) / 0.33 h / 27 °C 2: 91 percent / NIS / various solvent(s) / 0.42 h / 27 °C View Scheme

1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; lithium chloride / ethylene glycol dimethyl ether; water / 16 h / 80 °C / Inert atmosphere 2.1: tert.-butyl lithium / tetrahydrofuran / 2 h / -78 °C 2.2: 0.17 h / -78 °C 2.3: 1 h / 20 - 25 °C 3.1: VOF3; trifluoroacetic acid; trifluoroacetic anhydride / dichloromethane; ethyl acetate / 1.33 h / -78 °C View Scheme

1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; lithium chloride / ethylene glycol dimethyl ether; water / 16 h / 80 °C / Inert atmosphere 2.1: tert.-butyl lithium / tetrahydrofuran / 2 h / -78 °C 2.2: 0.17 h / -78 °C 2.3: 1 h / 20 - 25 °C 3.1: VOF3; trifluoroacetic acid; trifluoroacetic anhydride / dichloromethane; ethyl acetate / -78 - -10 °C View Scheme

N-benzyl-N,N,N-triethylammonium chloride; palladium diacetate; sodium hydrogencarbonate in N,N-dimethyl-formamide T=40°C; 24 h; Inert atmosphere;

magnesium in tetrahydrofuran 0.5 h; Heating;